Visible-light-induced synthesis of 2,4-disubstituted quinolines from o-vinylaryl isocyanides and oxime esters

被引：4
作者：
Liu, Yu [1 ]
Ding, Chuan [1 ]
Huang, Jia-Jing [1 ]
Zhou, Quan [1 ]
Xiong, Bi-Quan [1 ]
Tang, Ke-Wen [1 ]
Huang, Peng-Fei [1 ]
机构：
[1] Hunan Inst Sci & Technol, Dept Chem & Chem Engn, Yueyang 414006, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2024年 / 22卷 / 07期
基金：
中国国家自然科学基金;
关键词：
MULTICOMPONENT REACTIONS; CASCADE;
D O I：
10.1039/d3ob02060f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A visible-light-induced radical cyclization reaction of o-vinylaryl isocyanides and oxime esters to access various 2,4-disubstituted quinolines was disclosed. Oxime esters were employed as acyl radical precursors via the carbon-carbon bond cleavage. It provided an effective way for the synthesis of 2-acyl-4-arlysubstituted quinolines under mild conditions and exhibited good functional group tolerance and substrate applicability.
引用
收藏
页码：1458 / 1465
页数：8
相关论文
共 9 条
  • [1] Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines
    Huang, Peng-Fei
    Fu, Jia-Le
    Huang, Jia-Jing
    Xiong, Bi-Quan
    Tang, Ke-Wen
    Liu, Yu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (03) : 513 - 520
  • [2] Mn(III)-Mediated Regioselective 6-endo-trig Radical Cyclization of o-Vinylaryl Isocyanides to Access 2-Functionalized Quinolines
    Liu, Yan
    Li, Shi-Jun
    Chen, Xiao-Lan
    Fan, Lu-Lu
    Li, Xiao-Yun
    Zhu, Shan-Shan
    Qu, Ling-Bo
    Yu, Bing
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 688 - 694
  • [3] Visible-Light-Induced Intramolecular Tandem Cyclization of Unactivated Indoloalkynes for the Synthesis of Sulfonylated and Selenylated Indolo[1,2-a]quinolines
    Zhang, Shouren
    Yuan, Jinwei
    Huang, Guangchao
    Ma, Chengjia
    Yang, Jingjing
    Yang, Liangru
    Xiao, Yongmei
    Qu, Lingbo
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (16) : 11712 - 11727
  • [4] De Novo Synthesis of Imidazoles by Visible-Light-Induced Photocatalytic Aerobic Oxidation/[3+2] Cycloaddition/Aromatization Cascade
    Deng, Qiao-Hui
    Zou, You-Quan
    Lu, Liang-Qiu
    Tang, Zi-Long
    Chen, Jia-Rong
    Xiao, Wen-Jing
    CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) : 2432 - 2435
  • [5] One-pot synthesis of 2,4-disubstituted quinolines via three-component reaction of amines, aldehydes and alkynes using Al2O3 nanoparticles/methanesulfonic acid (nano-AMA) as a new catalyst
    Sharghi, Hashem
    Aberi, Mahdi
    Aboonajmi, Jasem
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2016, 13 (12) : 2229 - 2237
  • [6] Visible-Light-Induced Multicomponent Reaction of Aromatic Aldehydes, Amines and Sodium Difluoromethanesulfinate: Synthesis of CF2H-Substituted Secondary Amines
    Zhang, Shanshan
    Geng, Yang
    Jiao, Jialong
    Zou, Dapeng
    Wu, Yangjie
    Wu, Yusheng
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (23) : 4132 - 4137
  • [7] Visible-Light-Induced C(sp2)-C(sp3) Coupling Reaction for the Regioselective Synthesis of 3-Functionalized Coumarins
    Zhang, Ke
    Qiao, Li
    Xie, Jianwei
    Lin, Zhenwei
    Li, Hanjie
    Lu, Ping
    Wang, Yanguang
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (14) : 9552 - 9562
  • [8] Visible-Light-Induced Transition-Metal-Free Nitrogen-Centered Radical Strategy for the Synthesis of 2-Acylated 9H-Pyrrolo[1,2-a]indoles
    Yu, Wen-Qin
    Xie, Jun
    Chen, Zan
    Xiong, Bi-Quan
    Liu, Yu
    Tang, Ke-Wen
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (19) : 13720 - 13733
  • [9] Visible-Light-Induced Difluoroalkylation of 1-(Allyloxy)-2-(1-arylvinyl)benzenes and 1-(1-Arylvinyl)-2-(vinyloxy)benzenes: Synthesis of Bis-Difluoroalkylated Benzoxepines and 2H-Chromenes
    Zhou, Nengneng
    Xia, Ziqin
    Kuang, Kaimo
    Xu, Qiankun
    Zhao, Fangli
    Wang, Lei
    Zhang, Man
    ORGANIC LETTERS, 2022, 24 (31) : 5791 - 5796
1